“Fine. Here’s your stupid letter,” I said the next time we talked. “Can you please make the threatening emails go away? You’re scaring people.” “Yes. I’ll send it over to the tax team right away.”

The idea was to take everything that people hate about services like CorpNet and make it a pleasant, supportive experience for people. We’d answer their questions in words that made sense. We'd support them as they entered their tax IDs into their payroll system. If they got alerts from payroll or letters in the mail, we’d translate them into action.

I can’t stand it when people insist on unnecessary steps. Especially if those unnecessary steps are self-defeating.

This year, as you wallow in anxiety waiting for the tax team to get back to you, I have a fun project for you. Make sure your state payroll tax settings are correct. This is the only time when it DOESN’T feel irrelevant and boring. So Take advantage of it.

Your registered agent is just someone in another location that is authorized to accept mail for you. That's it.

If you work remotely for a company based in New York but you live and work outside of New York, then you pay taxes as if you're a New Yorker.

How does this even slip through? For THREE YEARS? Part of it had to do with a quirk of how taxes work in reciprocity states like Wisconsin. Part of it was because state agencies don’t talk to each other. And implementation teams aren’t tax experts. And some payroll providers don’t have enough error flags for situations like this. And humans are flawed. They make mistakes.

Have you ever wondered what it would be like if you threw five cats in a bag and asked them to run your payroll? Or have you already tried Paylocity?

You know why their checks are cut by ADP? Because most of them work at big, old companies and switching payroll providers is really, really hard at that size. And because people don’t know any better.

The PEO issues the paycheck, but you pay the wages, taxes, and employer portion of benefits. Since the PEO is the employer on paper, they handle registering for state agencies and tracking compliance laws. And because PEOs can pool all of their client-employees, you get access the more affordable and flexible large-group benefits.

Your dark and mysterious payroll past comes back into your life. Another notice. Something unreadable. You thought you'd left this all behind. But here it is again. Your pulse quickens. You're back under the tax agency's smoldering gaze. And this time, they won't take no for an answer.

Hey, Tyler. I noticed you have seven dependents on your tax form. Usually those would be people in your immediate family who share your living expenses and rely on your income, like a spouse and kids. Are you sure that all of these people would actually be considered dependents for tax purposes?

Deel is like if a pickup artist did payroll. Deel is the stereotypical tech-bro, “move fast and break (your) things,” the-rules-are-for-thee-and-not-for-me, all-glitz-no-substance disappointment. It looks pretty in the demo, even if those fancy buttons and cool apps never work as expected.

When you work overtime, you’re paid time and a half. The OBBBA only applies to the “and a half” portion of your pay. The OBBBA only applies to federal overtime, or hours worked beyond 40 hours in a week.

Many companies with fewer than 200 people will literally sign away legal control of their employees and pay multiple times more for payroll services. Just so they don’t have to think about state tax settings.

So your company’s In-N-Out reimbursement policy is a taxable benefit. But how do you tax a burger that's already in your belly? In payroll, this problem is solved with what’s called an “in-and-out.”

“I was disappointed to learn that I was paid the same as the guy checking receipts at Walmart.” He said in his annual self-review after getting a big, fat check.

Imputed pay is a type of non-cash benefit whose value is still taxable by the IRS. It could be life insurance, a domestic partner’s benefits, bills your employer paid for you, gifts. Answer: Your payroll person adds an “imaginary” dollar to your paycheck. That’s imputed pay.

I’m talking about the small business where an employee is on their spouse’s insurance or a Marketplace plan and the company just reimburses them for all or part of the premium like a regular business expense. You're not supposed to do that.

If you’ve been trapped in your workplace unable to leave, eating Doritos from the vending machine for dinner and sleeping under your desk, should you be paid for that time?